Windward Cay vacation rentals

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Discover a selection of 5 homes and other vacation rentals in Windward Cay that are perfect for your trip. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll have the amenities you expect and more, including parking and a TV. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Windward Cay

Showing deals for:Aug 14 - Aug 21

Image gallery for Cozy Family 4-Bedroom Bella Vida Home Near Disney World

Private Pool and SPA
9.0 out of 10, Wonderful, (63 reviews)
Wonderful
(63 reviews)

Cozy Family 4-Bedroom Bella Vida Home Near Disney World

Kissimmee

6% off
Price is $239
$1,673 for 7 nights
All fees included
Cozy Family 4-Bedroom Bella Vida Home Near Disney World

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Find out more about Windward Cay

Why visit Windward Cay

  1. Proximity to Theme Parks: Enjoy easy access to world-renowned attractions like Walt Disney World and Universal Studios, perfect for family fun.
  2. Outdoor Activities: Explore local parks, lakes, and nature trails, ideal for hiking, biking, and picnicking.
  3. Vibrant Local Culture: Experience the lively atmosphere at Disney Springs with shopping, dining, and entertainment options.
  4. Family-Friendly Amenities: Benefit from convenient facilities like nearby Walmart for all your vacation needs.
  5. Sunny Weather: Enjoy the warm Florida climate, perfect for outdoor adventures and relaxation throughout the year.

Top attractions near Windward Cay

Windward Cay in Kissimmee, Florida, is perfect for family-friendly outdoor vacations, offering a variety of attractions such as theme parks, lakes, and arts centers. Visitors can enjoy local highlights like Disney Springs and explore the vibrant culture and outdoor experiences the area has to offer. Whether you're traveling with family or friends, Windward Cay provides a delightful mix of entertainment and adventure for everyone.

  1. Walt Disney World® Resort: A magical theme park known for its iconic attractions and immersive experiences, offering entertainment for all ages. Enjoy enchanting rides, meet beloved characters, and create unforgettable family memories just 10 miles away from Windward Cay.
  2. Orange County Convention Center: A hub for culture, hosting various events and exhibitions. Explore art shows and conventions that highlight diverse creativity, located 8 miles from Windward Cay.
  3. Universal CityWalk: An exciting outdoor entertainment precinct featuring dining, shopping, and nightlife. Perfect for families looking for fun, this vibrant destination is 11 miles from Windward Cay.

Things to do recommended for couples

Looking for a romantic getaway in Kissimmee? Enjoy a fun round at Congo River Golf, indulge in a delightful dinner at Pirate's Dinner Adventure, and savor exquisite wines at True Blue Winery. Each experience is perfect for couples seeking adventure, romance, and unforgettable memories.

Things to do recommended for families

Your family will have a blast at Kissimmee Go-Karts, just 0.8 miles away, for some thrilling racing. For more sports excitement, head to ESPN Wide World of Sports Complex, 5 miles away. Don’t miss the fun at Aquatica waterpark, located 7 miles away, offering adventures for everyone!

What do I need to keep in mind when booking a vacation around Windward Cay

When planning your trip, whether you're traveling with a group, family, pets, or seeking extended stays, it's important to prioritize your preferences in your search. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Windward Cay with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Windward Cay with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Windward Cay: For many families, a vacation wouldn't feel complete without their furry companion by their side. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Windward Cay: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Windward Cay

Windward Cay in Kissimmee, Florida, offers a delightful vacation experience perfect for families and outdoor enthusiasts. With its welcoming atmosphere and sunny weather, explore nearby attractions like local parks and family-friendly entertainment. Don't miss the convenient amenities, including a nearby Walmart for your vacation needs. Whether you're seeking adventure or relaxation, Windward Cay is the ideal base for unforgettable excursions in the heart of Florida.

  • Seasons: Located a mere 0.6 miles from Windward Cay, Seasons is a vibrant neighborhood that caters to families and business travelers alike. The area is known for its excellent resorts and a variety of shopping venues. Visitors can indulge in cultural experiences at the local arts center and explore exciting nearby attractions such as renowned theme parks and a film studio. With a rich blend of entertainment options and family-friendly activities, Seasons is an ideal spot to create lasting memories.
  • Crystal Cove: Also situated 0.6 miles from Windward Cay, Crystal Cove offers a delightful mix of outdoor adventures and family-friendly entertainment. This neighborhood is home to inviting resorts and shopping areas, as well as well-maintained golf courses for enthusiasts. Close to major attractions like thrilling theme parks and a film studio, Crystal Cove is perfect for those looking to enjoy both leisure and excitement. The area's event conference venues also make it a great choice for business travelers.
  • Royal Palm Bay: Just 0.6 miles from Windward Cay, Royal Palm Bay is a charming neighborhood that attracts families and business visitors alike. With a variety of resorts, arts centers, and shopping options, there's something for everyone. The proximity to major attractions such as theme parks, event conference venues, and a convention center makes Royal Palm Bay a hub of activity. Whether you're seeking entertainment or a place to unwind, this neighborhood provides a welcoming atmosphere for all.

Best time to go to Windward Cay

If you're planning a trip to Windward Cay, it's a good idea to check both the weather and property rates. The warmest month is August.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudiness
January60.6°F (15.9°C)Light RainMostly Sunny
February64.4°F (18.0°C)Light RainMostly Sunny
March67.6°F (19.8°C)Light RainMostly Sunny
April72.7°F (22.6°C)Light RainMostly Sunny
May77.2°F (25.1°C)Light RainMostly Sunny
June81.1°F (27.3°C)Light RainMostly Sunny
July82.4°F (28.0°C)Moderate RainMostly Sunny
August82.6°F (28.1°C)Moderate RainMostly Sunny
September80.4°F (26.9°C)Moderate RainMostly Sunny
October75.2°F (24.0°C)Light RainMostly Sunny
November68.5°F (20.3°C)Light RainMostly Sunny
December64.4°F (18.0°C)No Rain (Dry)Mostly Sunny

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as this can lead to better prices. Plus, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, resume your previous arrangements, or manage your travel details. You'll find your saved or booked properties neatly organized into categories like Potential, Upcoming, or Current Trips. To begin utilizing Trip Boards, simply visit: https://www.vrbo.com/en-us/trips.

Frequently asked questions

What is the most popular type of vacation rental in Windward Cay?
In Windward Cay, vacation houses are the most popular type of rental, with about 17 available in the area. These properties often feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many also come with private outdoor areas, such as patios or gardens, where guests can relax after a day at the nearby attractions. Additionally, there are around 10 villas and several apartments and cottages, offering a variety of accommodations to suit different preferences.
Are there any beach house rentals in Windward Cay?
In Windward Cay, vacation rentals are available, with a focus on spacious private homes that cater to families and groups. These beach houses typically include multiple bedrooms, fully equipped kitchens, and outdoor spaces for dining and relaxation. Many properties also feature amenities such as private pools, game rooms, and proximity to local attractions like the nearby theme parks and natural reserves.
How much does it cost to rent a vacation home in Windward Cay?
Prices for vacation rentals in Windward Cay vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Windward Cay to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Windward Cay vacation house rentals?
You can find great discounts on house rentals in Windward Cay on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Windward Cay?
In Windward Cay, popular vacation rental amenities include fully equipped kitchens, allowing travelers to prepare meals at their convenience. Many rentals feature private pools, providing a refreshing option for relaxation and leisure. Onsite parking is typically available, making it easy for guests to explore the surrounding area with their vehicles. Additionally, rentals often come with coffee and tea makers for morning brews and outdoor decks or patios, superb for enjoying the pleasant Florida weather.
Can I find family house rentals in Windward Cay?
In Windward Cay, Florida, there are numerous family-friendly house rentals available—around 21 options for visitors to choose from. This charming community is ideally situated near the attractions of the Orlando area, making it a great base for families. Many of these properties come with spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces great for kids to play in. Common amenities include Wi-Fi and air conditioning, ensuring a comfortable stay for everyone.

Families can easily explore nearby highlights such as the Walt Disney World® Resort and Universal Studios, offering fun-filled days for all ages.
Can I rent a vacation home with a pool or hot tub in Windward Cay?
In Windward Cay, Florida, travelers can find a variety of vacation homes available for rent that feature pools and hot tubs, with around 27 options to choose from. This charming community is known for its close proximity to attractions like Walt Disney World®, making it an ideal base for families and groups. Many of the rentals come equipped with private pools, hot tubs, and outdoor lounging areas, great for relaxing after a day of exploring. Additionally, travelers can expect amenities such as fully equipped kitchens, spacious living areas, and game rooms in some properties, suiting both comfort and entertainment.
Are there any Windward Cay vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Windward Cay with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I book pet-friendly vacation rentals in Windward Cay?
In Windward Cay, there are several pet-friendly vacation rentals available, making it a great destination for travelers who wish to bring their furry companions along. Many of these rentals come equipped with amenities such as private pools, outdoor patios, and full kitchens, providing a comfortable and convenient stay. The area is known for its spacious properties, often featuring multiple bedrooms and living areas that cater to families or groups.

Windward Cay is located near various parks and recreational areas that welcome pets, allowing for enjoyable walks and playtime outdoors. The nearby Lake Buena Vista is an excellent spot for outdoor activities, and some vacation homes offer easy access to walking paths around the lake.
Can I find long-stay vacation rentals in Windward Cay?
A long-stay vacation rental in Windward Cay is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Windward Cay for a vacation rental?
The peak travel season in Windward Cay occurs from June to August, with July being the most popular month for vacation rentals. During this vibrant time, visitors flock to enjoy the warm sunshine and an abundance of outdoor activities. Whether it's lounging by the pool or taking part in water sports, the inviting climate ensures that guests can fully embrace the laid-back Florida lifestyle.

Temperatures in July typically range from the mid-70s to the low 90s Fahrenheit, offering ideal conditions for beach outings and sightseeing. Families and adventure seekers alike will appreciate the convenience of nearby attractions, from pristine beaches to exciting theme parks.

For those looking for a more budget-friendly option, consider visiting in October. This month offers pleasant weather and the added benefit of fewer crowds, allowing for a more tranquil experience. October is a wonderful time to explore the natural beauty of Windward Cay, with opportunities for scenic walks and enjoying the local flora and fauna.
Are there any remote work vacation rentals in Windward Cay?
In Windward Cay, Florida, there are numerous options for remote work vacation rentals, with about 27 properties available in the area. This charming community is conveniently located near the attractions of Kissimmee and Orlando, making it an ideal setting for those looking to balance work and leisure. Many of the rentals come equipped with essential remote work amenities such as high-speed Wi-Fi, dedicated laptop workspaces, and comfortable living areas conducive to productivity.

Travelers can find properties that feature modern kitchens, spacious dining areas, and outdoor spaces for breaks or relaxation. Additionally, some rentals may offer extra perks like pools or community amenities, providing a wonderful retreat after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Windward Cay vacation rental?
Book your Windward Cay vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Windward Cay, Florida, United States of America?
In Windward Cay, Florida, visitors can enjoy a variety of attractions that cater to families and outdoor enthusiasts. The nearby Kissimmee area is known for its proximity to major theme parks, including Walt Disney World®, which is just a short drive away. Additionally, the vibrant Old Town in Kissimmee offers shopping, dining, and entertainment, making it a great spot for evening strolls and family activities.

For nature lovers, the beautiful Lake Tohopekaliga is close by, offering opportunities for fishing, boating, and wildlife viewing. The area also features several parks and recreational areas, great for picnicking and outdoor sports.
Can I change or cancel my Windward Cay home rental booking on Vrbo?
To find Windward Cay vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Windward Cay vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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